3-Oxido-1H-imidazole-4-carboxamides
879
N-Methyl-1,5-dimethyl-3-oxido-1H-imidazole-4-carboxamide (1a). Yield 1.30 g (77%). Color-
less crystals, m.p. 229–231 °C (decomp.) (EtOH). IR (KBr): 3121 s, 1647 vs, 1599 vs, 1545 vs,
1457 m, 1409 m, 1373 m, 1324 m, 1285 m, 1162 m, 781 m, 757 m. 1H NMR (80 MHz,
CDCl3): 10.49 br. s, 1 H (NH); 7.83 s, 1 H (H-C(2)); 3.58 s, 3 H (NMe, imidazole); 2.94 d,
3 H, J = 5.6 (NHMe); 2.61 s, 3 H (Me). 13C NMR (50 MHz, CDCl3): 160.3 s (C=O); 131.0,
121.7 2s (C(4), C(5)); 125.9 d (C(2)); 31.9, 24.8, 9.1 3q (3 Me). EI-HRMS: 169.0857 (M+,
C7H11N3O2+; calculated 169.0851).
N-Methyl-1-butyl-5-methyl-3-oxido-1H-imidazole-4-carboxamide (1b). Yield 1.20 g (57%). Col-
orless crystals, m.p. 146–149 °C (CH2Cl2–Et2O). IR (KBr): 3093 m, 3018 m, 2958 m, 2933 m,
1653 vs, 1598 vs, 1564 m, 1469 m, 1419 m, 1370 m, 1287 m, 759 m. 1H NMR (200 MHz,
CDCl3): 10.13 br. s, 1 H (NH); 7.84 s, 1 H (H-C(2)); 3.68 t, 2 H, J = 7.3 (n-Bu); 2.74 d, 3 H,
J = 5.0 (NHMe); 2.41 s, 3 H (Me); 1.60–1.45 m, 2 H (n-Bu); 1.21–1.10 m, 2 H (n-Bu); 0.75 t,
3 H, J = 7.2 (n-Bu). 13C NMR (50 MHz, CDCl3): 160.2 s (C=O); 130.2, 122.0 2s (2 arom. C);
125.2 d (C(2)-H); 45.4, 25.1, 19.5 3t (3 -CH2-, n-Bu); 32.0, 13.4, 9.5 3q (3 Me). EI-HRMS:
211.1339 (M+, C10H17N3O2+; calculated 211.1321).
N-Cyclohexyl-1,5-dimethyl-3-oxido-1H-imidazole-4-carboxamide (1c). Yield 1.28 g (54%). Col-
orless crystals, m.p. 230–233 °C (decomp.) (EtOH). IR (KBr): 3088 m, 3027 m, 2931 vs,
2858 m, 1655 vs, 1605 vs, 1560 m, 1450 m, 1416 m, 1378 m, 1290 m, 758 m, 631 m,
602 m. 1H NMR (400 MHz, CDCl3): 10.56 br. d, 1 H, J = 7.2 (NH); 7.85 s, 1 H (H-C(2));
4.01–3.92 m, 1 H (cHex); 3.60 s, 3 H (NMe); 2.62 s, 3 H (Me); 1.95–1.92, 1.76–1.72 2m, 4 H
(cHex); 1.60–1.27 m, 6 H (cHex). 13C NMR (100 MHz, CDCl3): 158.7 s (C=O); 130.7, 122.4 2s
(2 arom. C); 125.2 d (C(2)); 47.2 d (CH, cHex); 32.8, 25.6, 24.6 3t (5 CH2, cHex); 32.1 q
(NMe); 9.5 q (Me). EI-HRMS: 237.1471 (M+, C12H19N3O2+; calculated 237.1477).
N-Allyl-1,5-dimethyl-3-oxido-1H-imidazole-4-carboxamide (1d). Yield 1.60 g (81%). Colorless
solid, m.p. 132–134 °C (acetone). IR (KBr): 3114 m, 3089 m, 2988 m, 1657 vs, 1641 s,
1602 vs, 1557 s, 1451 m, 1439 m, 1411 m, 1368 m, 1290 m, 754 m, 629 m, 606 m. 1H NMR
(80 MHz, CDCl3): 10.82 br. s, 1 H (NH); 7.78 s, 1 H (H-C(2)); 6.18–5.72 m, 1 H
(-CH2-CH=CH2); 5.40–5.04 m, 2 H (-CH2-CH=CH2); 4.14–3.96 m, 2 H (-CH2-CH=CH2);
3.58 s, 3 H (NMe); 2.62 s, 3 H (Me). 13C NMR (50 MHz, CDCl3): 159.4 s (C=O); 134.1 d
(-CH2-CH=CH2); 131.3, 122.0 2s (2 arom. C); 126.2 d (C(2)); 115.8 t (=CH2); 40.7 t (-CH2-);
32.2 q (NMe); 9.4 q (Me). EI-HRMS: 195.1019 (M+, C9H13N3O2+; calculated 195.1008).
N-Propargyl-1,5-dimethyl-3-oxido-1H-imidazole-4-carboxamide (1e). Yield 1.14 g (59%). Col-
orless crystals, m.p. 245–249 °C (decomp.) (EtOH). IR (KBr): 3214 s, 3112 m, 3042 m,
1652 vs, 1602 s, 1544 s, 1453 m, 1415 m, 1376 m, 1349 m, 1287 m, 739 s, 625 m, 603 m.
1H NMR (200 MHz, CDCl3): 9.72 br. s, 1 H (NH); 8.99 s, 1 H (H-C(2)); 4.20 dd, 2 H, J = 5.4,
2.5 (-CH2-); 3.75 s, 3 H (NMe); 2.63 s, 3 H (Me); 2.25 t, 1 H, J = 2.5 (-C≡CH). 13C NMR
(50 MHz, CDCl3): 158.3 s (C=O); 132.6, 121.3 2s (2 arom. C); 128.2 d (C(2)); 79.3 s (-C≡CH);
71.3 d (-C≡CH); 32.8 q (NMe); 28.3 t (-CH2-); 9.5 q (Me). EI-HRMS: 193.0862 (M+,
C9H11N3O2+; calculated 193.0851).
N-(2-Hydroxyethyl)-1,5-dimethyl-3-oxido-1H-imidazole-4-carboxamide (1f). Yield 1.17 g (59%).
Colorless crystals, m.p. 207–212 °C (decomp.) (EtOH). IR (KBr): 3163 vs (br.), 3115 s, 1652
vs, 1595 s, 1538 s, 1450 m, 1281 m, 1061 m, 756 m, 623 m, 607 m. 1H NMR (200 MHz,
DMSO-d6): 10.96 br. t, 1 H, J = 5.2 (NH); 8.41 s, 1 H (H-C(2)); 4.83 t, 1 H, J = 5.0 (OH);
3.56 s, 3 H (NMe); 3.48 t, 2 H, J = 5.1 (-CH2-); 3.33 t, 2 H, J = 5.6 (-CH2-); 2.50 s, 3 H (Me).
13C NMR (50 MHz, DMSO-d6): 159.5 s (C=O); 130.2, 120.4 2s (2 arom. C); 126.0 d (C(2));
59.9, 40.3 2t (2 -CH2-); 31.7 q (NMe); 9.0 q (Me). EI-HRMS: 199.0956 (M+, C8H13N3O3+; cal-
culated 199.0957).
Collect. Czech. Chem. Commun. 2010, Vol. 75, No. 8, pp. 871–885